1-Methylimidazole → (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

1-Methylimidazole (59.6 μl, 0.747 mmol) was added into the solution of (55)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid (150 mg, 0.374 mmol) in N,N-dimethylformamide (DMF) (2.7 ml). The resulting solution was cooled to 0° C., and then mesyl chloride (30.4 μl, 0.392 mmol) was added dropwise at 0° C. To the reaction mixture was added 5-fluoro-2-pyridinamine (46.1 mg, 0.411 mmol). After stirring for 2 h 10 min at ambient temperature, the reaction solution was purified by RP-HPLC to yield (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (104 mg, 0.210 mmol, 56% yield). MS (ES+) m/z 496.0 (MH+).

Provenance & Evidence